Iron(III) Triflate and γ-Cyclodextrin-Catalyzed Hydroarylation of Alkenes with 1-Naphthols and 2-Naphthols

Meng-Xue Hu; Peng Chen; Le-Wei Miao; Jianghuan Shi; Yi-Jun Jiang

doi:10.1055/a-2382-3010

Synlett, Table of Contents

Synlett 2024; 35(19): 2246-2250
DOI: 10.1055/a-2382-3010

letter

Iron(III) Triflate and γ-Cyclodextrin-Catalyzed Hydroarylation of Alkenes with 1-Naphthols and 2-Naphthols

Meng-Xue Hu‡

^aKey Laboratory of Advanced Mass Spectrometry and Molecular Analysis of Zhejiang Province, Institute of Mass Spectrometry, School of Material Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, P. R. of China

,

Peng Chen ‡

^aKey Laboratory of Advanced Mass Spectrometry and Molecular Analysis of Zhejiang Province, Institute of Mass Spectrometry, School of Material Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, P. R. of China

,

Le-Wei Miao

^aKey Laboratory of Advanced Mass Spectrometry and Molecular Analysis of Zhejiang Province, Institute of Mass Spectrometry, School of Material Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, P. R. of China

,

Jianghuan Shi

^bNingbo Institute of Measurement and Testing, (Ningbo Inspection and Testing Center for New Materials), Ningbo 315048, P. R. of China

,

Yi-Jun Jiang ∗

^aKey Laboratory of Advanced Mass Spectrometry and Molecular Analysis of Zhejiang Province, Institute of Mass Spectrometry, School of Material Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, P. R. of China

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Abstract

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Abstract

A Fe(OTf)₃ and γ-cyclodextrin-catalyzed hydroarylation of alkenes with 1-naphthols or 2-naphthols is demonstrated. This efficient and general method delivers a wide range of benzylic naphthols from readily available starting materials with high chemo- and regioselectivity in up to 99% yield, with no need for a strong base or additive.

Key words

naphthols - iron catalysis - cyclodextrin - hydroarylation - alkylation - alkenes

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References

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14 Benzylic Naphthols 3aa–fa and 4aa–ca; General ProcedureA oven-dried Schlenk tube was sequentially charged with the appropriate naphthol (0.125 mmol), γ-cyclodextrin (32.4 mg, 0.025 mmol), Fe(OTf)₃ (12.8 mg, 0.025 mmol), and DCE (2.0 mL), and the resulting mixture was stirred at 60 °C for 5 min. The appropriate alkene substrate (0.1875 mmol, 1.5 equiv) was then added, and the mixture was stirred at 60 °C for 4–8 h until the reaction was complete (TLC). The mixture was cooled to r.t. and the reaction was quenched with sat. aq NaHCO3 (40 mL). The resultant mixture was extracted with EtOAc (2 × 40 mL), and the combined organic extracts were washed with sat. brine (30 mL), dried (Na₂SO₄), and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, hexane–EtOAc).1-(1-Phenylethyl)-2-naphthol (3aa)Yellow oil; yield: 27.9 mg (90%). ¹H NMR (500 MHz, CDCl₃): d = 8.02 (d, J = 8.5 Hz, 1 H), 7.78 (dd, J = 8.5, 1.5 Hz, 1 H), 7.64 (d, J = 9.0 Hz, 1 H), 7.46–7.41 (m, 1 H), 7.37 (d, J = 8.0 Hz, 2 H), 7.34–7.28 (m, 3 H), 7.24–7.23 (m, 1 H), 6.97 (d, J = 8.5 Hz, 1 H), 5.16 (q, J = 7.5 Hz, 1 H), 4.93 (s, 1 H), 1.76 (d, J = 7.5 Hz, 3 H).1-[1-(4-tert-Butylphenyl)ethyl]-2-naphthol (3ae)White solid; yield: 31.9 mg (84%). ¹H NMR (400 MHz, CDCl₃): d = 8.04 (d, J = 8.4 Hz, 1 H), 7.76 (dd, J = 8.0, 1.6 Hz, 1 H), 7.62 (d, J = 8.8 Hz, 1 H), 7.46–7.41 (m, 1 H), 7.33–7.29 (m, 5 H), 6.97 (d, J = 8.8 Hz, 1 H), 5.14–5.04 (m, 2 H), 1.74 (d, J = 7.6 Hz, 3 H), 1.28 (s, 9 H). ¹³C NMR (151 MHz, CDCl₃): d = 151.8, 149.9, 140.4, 133.0, 129.8, 129.0, 128.8, 127.0, 126.7, 126.2, 123.9, 123.2, 122.7, 119.6, 34.5, 31.4, 17.3.

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